I can generate this file with some scripting language and then place it into the Asterisk Call File folder. The problem I'm having is: How do I call out to two numbers and join them in a conference call?

The MeetMe plugin/extension seems to be what I need in terms of conference calling, I'm just unsure as to how I'd use the two together and join them.

Also, is it possible to have multiple 2-person conference calls at the same time? Is setting this up as simple as setting aside X amount of 'channels' in the meetme.conf?

You've made this seem much easier than I first anticipated. I'm very new to Asterisk so I want some confirmation on my setup here - All I need to do is setup my sip.conf file, create the extensions.conf file and add your one DialOut context and then use the Call File to initiate the call? That's it? o.O
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HankMar 26 '10 at 0:31

If all you want is to connect two people together then that's pretty much it - you'll need to have some way of connecting to the outside world - a sip trunk or PSTN card, but it sounds like you've thought of that already.
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WhiskMar 26 '10 at 9:42